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Featured Apartments in Chestertown

Extended Stays Available Please Contact for Availability and Pricing

Located in the heart of Annapolis, this historic apartment building is within a 5-minute walk of Hammond-Harwood House and Annapolis City Dock. U.S. Naval Academy ...

4.8/5Exceptional! (34 reviews)
Great Location! Perfect Getaway

"This apartment was great for our short stay in Annapolis. Directly across the street from the Naval Academy and short walking distance from most of downtown. The only thing I will note, is that there is no onsite parking. As the city had cracked down on issuing permits to people unless it’s their ..."…"

Reviewed on Mar 30, 2020

Extended Stays Available Please Contact for Availability and Pricing
Amazing River House Waterfront Apartment on Choptank River on 18 Acre Farm

Located on the waterfront, this family-friendly apartment building is 5.9 mi (9.5 km) from Martinak State Park and 11.9 mi (19.1 km) from Adkins Arboretum. Delaware ...

4.9/5Exceptional! (36 reviews)
Great Get Away Location

"Peter and Helen are gracious owners who make you feel right at home! This is a perfect spot to relax and soak up the wonderful scenery on or off the river. Having access to the dock and kayaks was key for two boys to stay active throughout the day. We didn't know how much our dog enjoyed the water ..."…"

Reviewed on Aug 27, 2019

Amazing River House Waterfront Apartment on Choptank River on 18 Acre Farm
Historic & Quaint Room Downtown Middletown, DE

Situated in Middletown, this apartment building is 1.6 mi (2.5 km) from Frog Hollow Golf Club and within 6 mi (10 km) of Historic Houses of Odessa and Back Creek ...

Historic & Quaint Room Downtown Middletown, DE
Serene Waterfront Apartment on Kent Island

Situated in Stevensville, this apartment building is within 12 mi (20 km) of Sandy Point State Park, Chesapeake Bay Bridge, and Sandy Point Beach. Chesapeake ...

4.9/5Exceptional! (26 reviews)
Excellent Stay in Stevensville, MD

"We had a wonderful, relaxing, peaceful stay in Stevensville. The view of the bay was stunning. The neighborhood was so quiet, yet conveniently located. It was just a quick trip over the bridge to Annapolis. We toured The Naval Academy, enjoyed a bite to eat at the historic 1747 Reynolds Tavern and ..."…"

Reviewed on Feb 28, 2020

Serene Waterfront Apartment on Kent Island
Victorian on Main Street, Rock Hall MD. Walk to Everything! Sleeps 2-4

Situated in Rock Hall, this apartment building is within a 15-minute walk of The Mainstay and Rock Hall Harbor. Ferry Park is 1.4 mi (2.3 km) away.

4.8/5Exceptional! (10 reviews)
Rock Hall getaway

"This is our second stay in this property and hopefully not our last. We really like the location. The property is clean, the property manage is very nice The property is very clean, in excellent condition."…"

Reviewed on Jun 26, 2020

Victorian on Main Street, Rock Hall MD. Walk to Everything! Sleeps 2-4
Uniquely Historic & Quaint Room in the Center of Downtown Middletown,de

Situated in Middletown, this historic apartment building is 1.6 mi (2.5 km) from Frog Hollow Golf Club and within 6 mi (10 km) of Historic Houses of Odessa and ...

5/5Exceptional! (1 review)
Small but homey

"Communication with Andrea was excellent, she’d reply to any questions I had in less than 24 hours, and she is very hospitable! The property was as described except there is only one bathroom rather than two. My trip required lots of activity, on-the-go most of the time, so we basically needed a place ..."…"

Reviewed on Jun 27, 2019

Uniquely Historic & Quaint Room in the Center of Downtown Middletown,de
The Lodge on Main Street, a Victorian Apartment, Walk to Everything!

Situated in Rock Hall, this apartment building is within a 15-minute walk of The Mainstay and Rock Hall Harbor. Ferry Park is 1.4 mi (2.3 km) away.

5/5Exceptional! (6 reviews)
Lodge on Main

"We loved it! This was the second time we stayed there for the weekend (our annual Rock Fishing trip). The location is great (across from Java Rock, cute coffee shop). The property is very clean. Love the porch. Will not hesitate to reserve the Lodge for our next Rock Hall Vacation."…"

Reviewed on Jul 7, 2020

The Lodge on Main Street, a Victorian Apartment, Walk to Everything!
Historic & Quaint Room Downtown Middletown, DE Awaits You!

Situated in Middletown, this apartment building is 1.6 mi (2.5 km) from Frog Hollow Golf Club and within 6 mi (10 km) of Historic Houses of Odessa and Back Creek ...

Historic & Quaint Room Downtown Middletown, DE Awaits You!
Water view Hideaway on the Bay
Get Rates

Situated in Stevensville, this apartment building is within 12 mi (20 km) of Sandy Point State Park, Chesapeake Bay Bridge, and Sandy Point Beach. Chesapeake ...

5/5Exceptional! (1 review)
Beautiful Locale & Adorable, Comfy Lodgings

"Janet could not be a better hostess!! The walk to the bay is 30 seconds - 1 minute walk. Love that it is dog friendly!! Adorable inside and out."…"

Reviewed on Apr 9, 2020

Water view Hideaway on the Bay
Relax on the Eastern Shore of Kent Narrows in a King Bed

Situated in Grasonville, this romantic apartment building is within 3 mi (5 km) of Queenstown Premium Outlets, Queenstown Harbor Golf Links, and Queenstown Harbor ...

5/5Exceptional! (2 reviews)
6 Stars

"If there were 6 stars that wouldn’t be enough 😊�. The owner was extremely thoughtful and very accommodating. The Apartment was spotless and had every we needed."…"

Reviewed on May 3, 2019

Relax on the Eastern Shore of Kent Narrows in a King Bed
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Chestertown

Holiday Inn Express Hotel & Suites Chestertown
Holiday Inn Express Hotel & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $82 per night
4.4/5Excellent! (402 reviews)

"Extremely clean and appropriate precautious taken in response to COVID-19; some amenities missing (breakfast, fitness center, etc) as a result, but it was no issue. The staff was prompt and courteous. The property was ideally situated as well for our business in the area. I'd recommend to anyone ..."…"

Reviewed on Jun 28, 2020

Holiday Inn Express Hotel & Suites Chestertown
Great Oak Manor
Great Oak Manor
3.5 out of 5
10568 Cliff Rd, Chestertown, MD
The price is $199 per night
4.7/5Exceptional! (24 reviews)

"The view and the amenities made it worth the stay"…"

Reviewed on Jul 1, 2020

Great Oak Manor
Driftwood Inn
Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD
The price is $70 per night
2.2/5 (128 reviews)

"Convenient for Rock Hall triathlon event. Quiet (apart from triathletes talking outside). Room was clean and bed comfortable. Room had a microwave and bathroom was in good order."…"

Reviewed on Sep 29, 2019

Driftwood Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Staying in an Apartment in Chestertown

There are 9 lodging options in Chestertown. Though there aren't many apartments, we can help you find accommodations that are similar. When you search on Expedia, you can use the filters to search for a kitchen— just one of the conveniences you might find in an apartment. You can also filter by similar property types like vacation homes, condos, or cabins.

Here are some of the top apartments in the area:

Stay And Play In Downtown Annapolis:

  • Located in Annapolis , 26.2 mi/42.1 km from the city center
  • Includes a patio, a living room, and a fireplace

Global Luxury Suites at Toone Street:

  • Free WiFi, a washer/dryer, and a living room included
  • Located 25.7 mi/41.4 km away in Baltimore
  • An outdoor pool and a 24-hour fitness center on site

Global Luxury Suites at Brewers Hill:

  • It's located in Baltimore, 25.8 mi/41.6 km away
  • Includes free WiFi, a washer/dryer, and a living room
  • A 24-hour fitness center and a 24-hour business center on site

Relax on the Eastern Shore of Kent Narrows in a King Bed:

  • A fireplace included
  • Located 17.6 mi/28.4 km away in Grasonville

Waterfront Apartment Kent Island. Close to Wedding Venues:

  • Located in Stevensville , 23.6 mi/38 km from Chestertown
  • Includes a patio and a living room
  • A fitness center and a spa tub on site

When is the Best Time to Visit Chestertown?

Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay. Since apartments often have more stringent cancellation policies, it’s good to familiarize yourself with these seasonal weather averages before booking.

  • The hottest months are typically July and August, while January and February are the coldest months
  • January-March: Daytime temperatures average 58° F and nighttime temperatures average 25° F
  • April-June: 85° F is the daytime average and 39° F is the nighttime average
  • July-September: Daytime averages are around 87° F and nighttime averages are around 53° F
  • October-December: The average temperatures are 73° F during the day and 28° F at night
  • Average rainfall is 1.42 inches in a year

Things to Do in Chestertown

Cultural attractions include Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland, whereas Wilmer Park is one spot to enjoy nature. Washington College and Rolphs Wharf Marina are a couple of places you'll find in the larger area.

Chestertown is known also for its:
  • Sports
  • University life
  • Festivals
  • Boating
  • Historical sites
  • Art
  • Wildlife

How to Get to Chestertown and Around the Area

Fly into Baltimore, MD (MTN-Martin State), which is located 19.5 mi (31.4 km) away. Otherwise, look for flights into Easton, MD (ESN-Easton - Newnam), which is 27.3 mi (43.9 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
There are 15 lodging options in Chestertown. Though there aren’t many apartments, we can help you find similar accommodations. When you search on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. Even filter by similar property types like vacation homes, condos, or cabins.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
Listed below are some of the top apartments in the area to choose from: The Lodge on Main Street, a Victorian Apartment, Walk to Everything!: Situated in Rock Hall, 8.9 mi/14.3 km from the heart of Chestertown. Includes separate living rooms and in-room sofa beds. Amazing River House Waterfront Apartment on Choptank River on 18 Acre Farm: Located 24 mi/38.7 km away in Greensboro. Private patios, separate living rooms, and fireplaces are included. Access to a game room is available on site. Victorian on Main Street, Rock Hall MD. Walk to Everything! Sleeps 2-4: It’s located in Rock Hall, 8.9 mi/14.3 km away. Extended Stays Available Please Contact for Availability and Pricing: 26.2 mi/42.1 km away in Annapolis. Private patios, separate living rooms, and fireplaces are included. Historic & Quaint Room Downtown Middletown, DE: It’s situated in Middletown, 26.2 mi/42.2 km from Chestertown.
What's the weather like in Chestertown?
Though weather is just one aspect, it can have an impact on your travel plans, especially if you have a long stay planned. The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 39°F. Average annual rainfall for Chestertown is 42 inches.
What should I see and do in Chestertown?
Cultural attractions include Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland, whereas Wilmer Park is one spot to enjoy nature. In the larger area, you’ll find Washington College and Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Fly into Baltimore Washington Intl. Thurgood Marshall Airport (BWI), which is located 30.8 mi (49.6 km) from the heart of the city. Otherwise, you can search for flights to Baltimore, MD (MTN-Martin State), which is 19.5 mi (31.3 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.

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